Abstract
Catalytic asymmetric aziridination of aryl imines
Highlights
Aziridines are important intermediates in organic synthesis
Chiral boronate catalysts derived from this set of six ligands 6 - were formed in situ and used to screen the aziridination of N-(4-bromobenzylidene)benzhydrylamine with ethyl diazoacetate (Scheme 2)
The catalysts derived from steroidal-type binaphthol ligands 9 - 11, while providing aziridine 13 in good yields, gave levels of asymmetric induction similar to those observed with the parent binaphthol.[10,11]
Summary
Aziridines are important intermediates in organic synthesis. SN2 ring opening reactions, for example, result in substituted amines, diamines, amino alcohols, and α- or β-amino acids.[1]. Chiral boronate catalysts derived from this set of six ligands 6 - were formed in situ and used to screen the aziridination of N-(4-bromobenzylidene)benzhydrylamine with ethyl diazoacetate (Scheme 2). The catalysts derived from steroidal-type binaphthol ligands 9 - 11, while providing aziridine 13 in good yields, gave levels of asymmetric induction similar to those observed with the parent binaphthol (entries 1 - 4).[10,11] as expected, increasing the steric effect by introducing bulky substituents in the 3- and 3'-positions of the binaphthol scaffold resulted in an increase in the enantioselectivity of the addition.
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